Methanol → [5-Biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazol-3-yl]methanol

HRID 1797120

反応式

HRID 1797120 の反応式
C([O:8][CH2:9][C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[C:13]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[N:12][N:11]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.CCCCCC.CO.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:25]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:26]=[CH:27][C:22]([C:13]2[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])[C:10]([CH2:9][OH:8])=[N:11][N:12]=2)=[CH:23][CH:24]=1

参加物

6

反応物 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 220192303-Benzyloxymethyl-5-biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazoleHCID 22019253Boron trichloride hexane

生成物 1

HCID 22019266[5-Biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazol-3-yl]methanol収率 44%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

3-Benzyloxymethyl-5-biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazole (6.00 g) was dissolved in chloroform (200 ml), followed by dropwise addition of 1 mol/liter boron trichloride-hexane solution (30 ml) at −44° C. and stirred at the same temperature for 30 minutes and at ambient temperature for one hour. To the reaction solution were added methanol (5 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml), followed by concentration under reduced pressure. To the resulting residue were added tetrahydrofuran (100 ml), aqueous 2 mol/liter sodium hydroxide solution (100 ml) and tetrabutylammoniumhydrogensulfate (0.10 g), and stirred at ambient temperature for 12 hours. The reaction solution was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting residue was purified by silica gel chromatography (eluent: chloroform/methanol=96/4) and recrystallized from a mixture solution of n-hexane-ethyl acetate-ethanol, to afford the entitled compound as white crystal (2.09 g, 44%). The physico-chemical values are as follows.

後処理

  1. concentrationfollowed by concentration under reduced pressure
  2. additionTo the resulting residue were added tetrahydrofuran (100 ml), aqueous 2 mol/liter sodium hydroxide solution (100 ml) and tetrabutylammoniumhydrogensulfate (0.10 g)
  3. stirringstirred at ambient temperature for 12 hours
  4. extractionThe reaction solution was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customAfter the solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by silica gel chromatography (eluent: chloroform/methanol=96/4)
  8. customrecrystallized from a mixture solution of n-hexane-ethyl acetate-ethanol

出典と根拠

ORDレコード
ord-99be062e11774de7a1c62c1492578792
出典データセット
uspto-grants-2006_04
特許番号
US07034047B2

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